The Thrilla in the Villa: Inside the World of Luxury Vacation Rentals

What's your desire? A rose-strewn driveway? A soccer star to coach your little darling? Your very own domed observatory? Welcome to the wild, money-run-amok world of luxury vacation rentals.

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Jean-Philippe Delhomme

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By Lauren Lipton

Mar 13, 2015

The Saudi prince wanted a winter wonderland. He was yearning for a romantic European Christmas à deux, complete with roaring fire, big gifts in little boxes, and lavish holiday decor. There was just one obstacle: It was October.

The woman with whom he would be vacationing "was not his wife, you see," says Sylvia Delvaille Jones, founder of Villas & Apartments Abroad, which sets up travelers in luxurious vacation rental homes all over the globe. Because December 25 was reserved for family, the prince wished to celebrate in advance with his leggy Welsh mistress. Could Jones make Christmas come early?

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She could. She contacted the owner of the 12th-century Water Castle in Lower Austria. "We both laughed," Jones says, "and then she got all her friends to come dress her castle with lights, richly decorated trees—the whole nine yards." The prince and his mistress were able to enjoy a storybook holiday two months early in "their own" beautifully appointed home.

For travelers who crave total privacy, unique amenities, and personalized service beyond their wildest dreams, private villas are the new five-star hotel. More than a third of vacationers with annual household incomes of $500,000 or more stayed in a rental home in the past two years, and nearly half were interested in that option as an alternative to a hotel for future trips, according to a 2014 survey by MMGY Global, a Kansas City travel and hospitality marketing firm.

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It's not hard to see why. Increasingly, the villa—loosely defined as a stand-alone property rented to a single guest or group at a time—has come to define everything moneyed vacationers are looking for. Whether a centuries-old European estate, a modern beachfront mansion, or a self-contained island compound, the best villa offers all of the comforts of someone else's home.

Staying in a private villa is about "getting something that you otherwise don't have access to," says Mara Solomon of Homebase Abroad, which specializes in historic Italian properties, "because it doesn't exist anywhere else. It is the best of everything from centuries—every single silk on the wall, every single fitting in the bath- room, every single piece of art or antique, down to the family's own china of the most extraordinary quality."

As do similar companies', Homebase Abroad's guests make up, Solomon says, "a percentage of the one percenters" in the United States and other parts of the globe. They run the gamut from the phenomenally rich and/or famous seeking total seclusion and safety to prosperous, multigenerational families that want to play house en masse, to groups gathering for important milestone celebrations. Another common demographic: adult friends, such as Solomon's client New York fashion designer Dennis Basso, who organized an Italian villa rental last summer with his husband Michael Cominotto and four other couples. The property, Villa di Torno, is a neoclassical waterfront home from whose rooms one can hear the gentle lapping of Lake Como against the private dock, directly below. There are a chef, a housekeeper, and a laundress, and two housemen/waiters; Basso's group also had a captained boat at their disposal day and night.

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"It was amazing," Basso says. "I always say, 'If it's not going to be equal, better, or more interesting, I would then prefer to stay at home.' "

Because Basso isn't the only guest who feels this way, the boutique agencies that handle these properties do much more than just accept security deposits and pass over the house keys. Increasingly, these firms, as well as some of the properties' gracious and accommodating owners, have carved a niche for themselves by granting requests from villa guests that range from the low-key to the lavish.

Jean-Philippe Delhomme

For Elizabeth Dorros, an events manager in New York City, a trio of milestone family birthdays during a single week in May 2013 had her puzzling over how and where to entertain 30 members of her well-traveled clan, who were expecting a once-in-a-lifetime spectacular. Dorros contacted Marina Gratsos of Carpe Diem Luxury Travel, a London company specializing in glamorous excess. Gratsos not only arranged for the group to stay together at two private residences in Umbria over the course of a week, she put together a party at each. The first was a 70th birthday fete set against the picturesque medieval and Renaissance ruins on the estate grounds; it included jugglers and flag wavers in period costume. The second, celebrating the 40th birthdays of Dorro's husband and his cousin, centered on a wine-stomping competition—even though grapes were out of season.

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"Marina still made it happen," Dorros says. "The entire family dove into barrels fit for 20 people, rolling up white linen pants and beautiful silk summer dresses, which were getting splashed with grape juice."

On the last night Gratsos organized a private home performance by local opera singers, and members of the villa staff concluded the evening by breaking into an impromptu rendition of "Memory" from Cats. Dorros's family was bowled over. So was Dorros—who now works as Carpe Diem's U.S. liaison. "We understand all angles of a client's needs and requests, no matter the level of demand," she says.

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For these companies many requests are fairly easy to fulfill. In Italy, Countess Simonetta Brandolini d'Adda, who represents about 70 for-rent estates (mostly owned by her friends), can arrange a private dinner in front of the David statue at the Accademia Gallery in Florence, or a visit to a fresco or sculpture restoration project in progress. "People love to go up on the scaffolding," she says.

Other villa agencies, in places ranging from Europe to Greece to the Caribbean to California, connect guests to locals for a more authentic experience. There have been cooking lessons with private chefs, mushroom-foraging outings with expert mycologists, and excursions to tiny out-of-the-way farms, cheesemakers, and wineries. A local host in Croatia, upon hearing that her American visitors had roots in the country, spent hours tracking down two of their relatives and served as translator at a traditional meal for the long-lost family members. The reunited kin are still in touch.

There's also an entire category of child-related requests, from keeping kids entertained—say, by arranging to have a local professional soccer player drop in and put them through their paces—to simply making sure they're safe and calm. That might mean having a property thoroughly babyproofed, ridding the pantry of any foods to which the little darlings are allergic, or even ensuring that the children are never without their preferred brand of coconut water.

That last, in fact, is a routine requirement for Holly Cao and Bob Hellman. The Atherton, California, parents, who are both in private equity, frequently stay in villas from a company called Exclusive Resorts. To keep their twins, Tucker and Carter, three, well rested and on schedule, the couple enlists the company's concierge team to help recreate the kids' room at home, including bedding, sound machine, stuffed animals, photographs, and familiar smells. "There's an unbelievable number of things we've asked for," Cao says. "But traveling with young kids, any little thing could cause a disaster."

Calamity was averted during a 2014 villa vacation in Maui, thanks to the on-site concierge. Before the family arrived, he went looking for Harmless Harvest 100% Raw Coconut Water, the discerning toddlers' favorite. (It's one of the few brands, Cao explains, that tastes like real coconut.) But it wasn't available in Hawaii. Thinking on his feet, the concierge bought 25 fresh coconuts. "He had them cracked and the coconut water put in a jug for us in the fridge, and it was ready to go," Cao says. "Crazy, right?"

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Not as crazy as some requests. The staff of a villa in the Sri Panwa development on Phuket, in Thailand, once delivered 30 bottles of Louis Roederer champagne to a high-profile guest celebrating an anniversary. The staff, naturally, didn't ask what one couple was going to do with so much bubbly. Housekeeping came into the room the next morning to find the tub filled with it.

And for a wedding several years ago at the villa Don Arcangelo all'Olmo in Sicily, the Thinking Traveller, a London company that specializes in Mediterranean properties, had a 1,000-pound Steinway concert piano trucked in so that Lang Lang, the world-renowned pianist, could play it at the event.

Even those assignments were garden variety compared to this request from a couple who stayed for a month last summer at Villa Nel Bosco in Sonoma County, California. The Manhattan foodies had always dreamed of preparing meals with vegetables picked from their own garden. They wondered if the agency could plant one and even supplied a list of their desired crops: heirloom tomatoes, arugula, green peppers, broccoli, onions, various lettuces, herbs, peaches, and strawberries.

Jean-Philippe Delhomme

None of this would have been a problem, except that the guests were due in two weeks and the seeds hadn't even been sown. So the agency scoured the area's growers for fully developed plants, including a peach tree. They had garden beds, an irrigation system, and deer fencing installed. By the time the couple arrived, the garden was perfect, if ever so slightly jerry-rigged. "When you're moving plants, they don't always arrive intact," Liza Graves, of Beautiful Places, says. "We were trying to get the pepper plants symmetrical, and one or two peppers had fallen off. Yes, there was Krazy Glue involved."

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While the concept of omnipotent specialists who can make a garden grow overnight is relatively new, villa travel isn't. It has its roots in the centuries-old custom of the Grand Tour, in which members of the British ruling class would travel for months or years through Europe, snapping up paintings, antiquities, and other pricey souvenirs, a practice later embraced by the American upper class as well. Discrimi- nating sojourners recognized the charms of the villa, in which, Henry James wrote in his Gilded Age travelogueItalian HoursItalian Hours, one "might live over again in them some deliciously benighted life of a forgotten type—with graceful old sale, and immensely thick walls, and a winding stone staircase, and a view from the loggia at the top; a view of twisted parasol-pines balanced, high above a wooden horizon, against a sky of faded sapphire."

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The modern iteration of villa travel began to take off as a trend about three or four years ago, around the time Airbnb, the $10 billion online business that allows users to list and lease their apartments or houses, became the most talked-about development in bargain travel. Though they tend to attract different ends of the market, Airbnb accommodations and exclusive villas share a similar appeal. Private residences can offer a deeper experience of a location, often away from the typical tourist destinations. They're also often found in places hotels can't penetrate. In Sonoma County, for example, it would be extremely difficult for a variety of reasons to "build a new hotel with 200 rooms on top of a hill in wine country with an amazing view," says Graves, of Beautiful Places. But you can have that with a private estate.

Some observers warn that this trend has a dark side. The historian and lecturer William Howard Adams says villa travel only accentuates the "totally depressing" gulf between those who gobble up every possible extravagance, the subordinates who indulge them, and the teeming, impoverished multitudes from whom they isolate themselves. "It takes us back to the days of Rome, except that the rich are richer now than anyone could possibly imagine," says Adams, the author of On Luxury: A Cautionary Tale, a reflection on the morality of excess. An arrangement in which a tiny minority is able to demand and get anything it wants—"a whole system built on absolutely limitless consumption"—can't last, he says. And the idea that one can segregate oneself in a plush fortress is an illusion anyway. "It's trying to control your environment completely," he says. "But you can't control anything once you get beyond the boundaries of the villa. There are too many uncertainties."

Nevertheless, the trend continues. Eight percent of people worth at least $1 million, and almost 30 percent of those worth more than $25 million, spend $25,000 or more a year on leisure travel, according to Spectrem Group, a consulting firm in Illinois. Five percent of the latter group shells out $100,000 or more.

To attract that kind of spender, a number of upscale hotel chains are adding villa-style accommodations to appeal to discriminating, deep-pocketed guests. Four Seasons Hotels and Resorts recently appended "and Residences" to the titles of its properties in Vail, Jackson Hole, and Whistler. (Each already included separate villa-like accommodations and wanted to be sure potential guests knew it.) The upscale chains Viceroy Hotels & Resorts and Rosewood Hotels & Resorts are also adding villa options.

While hotels are cribbing from the villa business, the villa business has learned a thing or two from hotels—in particular, branding. In April 2015 an invitation-only consortium of exclusive agencies and some individual properties will launch a new partnership called Ultra-Villa. The idea is to guarantee a certain level of quality—to be the Relais & Châteaux of the villa world. That may come in handy when a villa stay doesn't go as planned, as James Martin, a New York businessman, discovered during a trip to Buenos Aires a few years ago. He and his friends had rented an "amazing" $30 million property and were on their way to it when they got a call from their rental specialist: The house had burned down in an electrical fire. "It was a big, smoldering pile of ash," Martin says. Though nobody had been hurt, there was still the question of where Martin and his group would stay. His agency scrambled to find them a series of houses along the Rio de la Plata.

"Of course, these homeowners had not been prepared for guests, so we literally went in with their laundry still in the washing machines," Martin recalls. "It makes for a good story."